Carbon tetrabromide → HCID 15887274, compound

HRID 2187040Notes

Reaction equation

HRID 2187040 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][C@@:6]12[CH2:17][CH2:16][CH2:15][C:13]3[C:14]1=[C:9]([CH:10]=[CH:11][CH:12]=3)[NH:8][C:7]2=[O:18].C(Br)(Br)(Br)[Br:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[Br:20][CH2:2][CH2:3][CH2:4][CH2:5][C@@:6]12[CH2:17][CH2:16][CH2:15][C:13]3[C:14]1=[C:9]([CH:10]=[CH:11][CH:12]=3)[NH:8][C:7]2=[O:18]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 70155508HCID 70155508, compound

Product 1

HCID 15887274HCID 15887274, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(S)-2a-(4-hydroxybutyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one (1.96 g, 8.0 mmol) was dissolved in acetonitrile (50 ml). Then, carbon tetrabromide (3.31 g, 10.0 mmol) and triphenylphosphine (2.72 g, 9.6 mmol) were added to the resulting solution and stirred at room temperature for four hours. The solvent was evaporated from the reaction mixture, and ethyl acetate, water and hydrochloric acid (1N) were added to the resulting residue. The reaction product was extracted with ethyl acetate, and the extracted product was washed with saturated saline solution, successively dried over anhydrous sodium sulfate, followed by evaporating the solvent. The resulting product was separated and purified by means of silica gel column chromatography, whereby 2.40 g (yield 97%) of the above-described object compound could be obtained.

Workup

  1. customThe solvent was evaporated from the reaction mixture, and ethyl acetate, water and hydrochloric acid (1N)
  2. additionwere added to the resulting residue
  3. extractionThe reaction product was extracted with ethyl acetate
  4. washthe extracted product was washed with saturated saline solution
  5. dry with materialsuccessively dried over anhydrous sodium sulfate
  6. customby evaporating the solvent
  7. customThe resulting product was separated

Sources & evidence

ORD record
ord-8e60181c90c04198b149e2b3d134ef5c
Source dataset
uspto-grants-2002_06
Patent number
US06407112B1

Reaction notes

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